Findings on contextual variables related to subjective well-being (SWB) and gratitude among adolescents are inconsistent. This study examined the association between SWB and gratitude among a group of South African adolescents (n = 840) as well as gender and cultural differences in the mean scores on measures of SWB and gratitude. Correlations between SWB and gratitude were in the expected direction. Females showed higher levels of satisfaction with school, friends, and self, compared with males, and also higher levels of negative affect, state, and trait gratitude. Black adolescents were more satisfied in the domains of self and school and showed higher levels of state gratitude. White adolescents experienced higher levels of general life satisfaction and satisfaction with living environment, as well as trait gratitude. Programs to enhance youth well-being could benefit from focusing on specific life domains and affective experience to better address the needs of specific groups of adolescents.